Wholesome Pleasures

In the Theravadin Buddhist tradition, the compulsive pursuit of pleasure is a hindrance (nivarana) to access collectedness (upacara samadhi) necessary for acquiring insight (panna, vipassana). Experiencing pleasure, strictly speaking, is not a hindrance. Instead, strictly speaking, a hindrance occurs only when it displaces or delays the experience of upacara samadhi. If the cemetery contemplations or the meditation on the repulsive parts of the body does not temporarily suspend your automatic pursuit of sensuous pleasure, then many months or even years of mindfulness meditation and monastic seclusion may be required to help you settle for more subtle sources of comfort and peace. There is no blame to be assigned because of a strong need for sensuous pleasure, because it is caused by a previous experience of great and tragic suffering. As you suggest, there are many meditation practices that are pleasant or even blissful. The answer to your question is “yes.” But, be certain that indifference to or “detachment” from pleasure of all kinds is not a path to Enlightenment.

(I hope you don't mind this theoretical answer to a personal-practice question.)

Apart from meditation and the bliss (sukha) of quieting and cessation, I think that it (i.e. "what provides wholesome pleasure") may be "skillful virtue" or "wholesome action" (i.e. kusala sila) -- see for example What are the benefits of practicing Sila?

Maybe it does but I don't think that Buddhism teaches "subjectivity" in that context: instead it uses words like "virtuous", "skillful", "wise", perhaps "noble" (and, at least initially, maybe "blameless" or even "praiseworthy" too).

The "subjective pleasure" you defined sounds just about OK, however:

• Harmless is virtuous and not bad, but maybe benevolent and unselfish is even better?
• "An activity one enjoys" is all very well, but (for example) some of the suttas which talk to monks about food say that food should be taken not as a sensual pleasure or craving but rather with the intention of ending sensation (i.e. to end a feeling of hunger, not to replace a feeling of hunger with a feeling of fullness), and for the purpose of living the holy life.

To try to relate that to personal experience, I gather from previous questions that you're looking for activities which provide "wholesome pleasures", to replace other "addictions" which you don't feel are wholesome. Perhaps that hints at a definition of what you consider to be "wholesome activity": i.e. they're actions that you don't regret, action whose reward is "freedom from remorse".

The canonical reference case for "wholesome pleasure" is Buddha's entering jhana by remembering how he sat under blossoming trees back when he was a child (can anyone find the actual sutta?) In my understanding, before that turnaround occurrence Buddha-to-be was excessively strict to oneself and did not allow even a slightest indulging in pleasant mental states.

So in traditional Buddhism "wholesome pleasure" refers specifically to jhana, also known as "pleasant abiding in the here and now". (Specifically, the first jhana is about joy generated deliberately by reflecting on one's actual wholesome qualities and spiritual realizations. This reflection is what's technically referred to as vitakka/vicara. Vitakka is the act of deliberate recollection of a particular point, and vicara is the reflection moment, to let the effects of the recollection permeate the mind. And then the subsequent jhanas are progressively more refined states of pleasant abiding centered around subjective feelings of wellness.)

In Mahayana, wholesome pleasure can be defined more broadly as any activity that leads to harmony and well-being, such as recreation in nature, sports, or arts.

To answer your question, we need to go back to the first principles - the noble truths and more broadly the principle of "this-that conditionality" (idappaccayata). The sukha/dukkha modality of emotions is driven primarily by a measure of match or mismatch between one's expectations of how things "should be" and one's evaluation/interpretation of actuality. So both suffering and satisfaction are always subjective, always - and come from our own subjective interpretation not only of the expectations but also of the actuality.

So in theory, satisfaction could be generated by adopting a completely arbitrary set of expectations and interpretations, as long as they match. However in practice, Buddha recognized that sentient beings do not exist in isolation from their environment. The environment cannot be arbitrarily changed. Therefore, to achieve permanent Nirvana in practice, we have to find a way to match our expectations and interpretations that would be compatible with existing environment. If one's frame of reference goes against the reality and the laws of nature, one will inevitably fall out of Nirvana, since suchness cannot be contrived in the face of an obvious conflict with facts.

This is why Buddha said that his Dharma is good in the beginning, good in the middle and good in the end. For Dharma (here defined as a set of expectations and interpretations that frames a way of living and acting) to be holistic it must be in sync with the laws of nature, and the ethics&laws of society (assuming the latter developed from the seeds present in the first). This very important requirement is reflected in the unity between Buddha's ethical teaching and his primary, soteriological teaching. Buddha's suchness is holistic, because it sits on the foundation of physiologically/psychologically healthy and the socially "blameless".

I hope this makes sense. To summarize this in context of your question, pleasure is always subjective, and you are free to find your own creative ways to match "expectations" and "interpretation of actuality" - as long as you remain in sync with the reality of nature (i.e. you do not destroy your physical body) and with the laws/ethics of society (don't create causes for future suffering).

One last caveat. Buddha states very clearly in the 2nd Noble Truth that attachment to any permanent state remains the primary factor of suffering, and this includes addiction to the pleasure of jhanas. So just remember that whatever contrived pleasure-generating mindsets you employ, they can at best only be used as a form of recreation, they are not the permanent liberation. That said, the ability to be independent of circumstances in generation of one's own pleasure, satisfaction, and peace, is an important step towards true homelessness/baselessness of suchness, the permanent unconditional Nirvana.

"what provides wholesome pleasure and joy in a context of mental states and Buddhism?"

In general, anything that weakens greed, aversion and delusion is a potential source of wholesome pleasure.

From the suttas....

Abandoning what is unwholesome is a source of pleasure (AN 2.19):

because this abandoning of what is unskillful is conducive to benefit and pleasure, I say to you, ‘Abandon what is unskillful.’

Similarly, the practice of sīla (the virtue group of the noble eightfold path) incurs in wholesome pleasures (AN 10.1):

“Ānanda, the purpose and benefit of wholesome virtuous behavior is non-regret.”
“And what, Bhante, is the purpose and benefit of non-regret?”
“The purpose and benefit of non-regret is joy.”

...which continues in a chain leading to jhāna and, further on, liberation. In the context of meditation, jhāna is specifically said to be a superior pleasure compared to sensual pleasures (SN 36.19) and, for example, seclusion and samadhi are sources of pleasure (in the first and second jhānas).

Also, the following are benefits associated with wholesome pleasure obtained when metta practice "has been pursued, developed, and cultivated, made a vehicle and basis, carried out, consolidated, and properly undertaken" (AN 8.1):

(1) “One sleeps well; (2) one awakens happily; (3) one does not have bad dreams; (4) one is pleasing to human beings; (5) one is pleasing to spirits; (6) deities protect one; (7) fire, poison, and weapons do not injure one; and (8) if one does not penetrate further, one moves on to the brahmā world.

Particularly, the abandoning of sensual pleasures (unwholesome) in favor of exclusive wholesome pleasures is taught in accordance with one's commitment. In this case, for those who enjoy sensual pleasures, the Buddha taught four kinds of happiness that may be achieved: "The happiness of ownership, the happiness of enjoyment, the happiness of freedom from debt, and the happiness of blamelessness" (AN 4.62).

Also, the Buddha said that "Longing and unrighteous greed are a defilement of the mind" and taught them the proper way of gaining wealth, fame, long life, and a happy destination after the break up of the body (AN 4.61).

Thus, the preservation of the precepts, the practice of sīla, and teachings such as the ones above are the proper ways (i.e. according to the Dhamma) to engage in "an activity one enjoys which isn't harmful" and "fulfilling ambitions linked to one's aspirations".

"And, again from the perspective of mental states, is happiness always reliant on subjectivity to a degree? Here, I mean to ask whether one's mood, or personal interest, or one's personality always play a part in generating pleasure and joy (aside, perhaps, from in meditation)?"

Sure. For example, while a certain person may find herself delighting in, say, virtuous behavior, someone else may not. Some people may delight in concord while another may delight in discord (MN 41). Finally, some people find peculiar things as source of pleasure:

“What, bhikkhus, is the way of undertaking things that is pleasant now and ripens in the future as pain? Here, bhikkhus, someone in pleasure and joy kills living beings, and he experiences pleasure and joy that have killing of living beings as condition. In pleasure and joy he takes what is not given… holds wrong view, and he experiences pleasure and joy that have wrong view as condition. On the dissolution of the body, after death, he reappears in a state of deprivation, in an unhappy destination, in perdition, even in hell. This is called the way of undertaking things that is pleasant now and ripens in the future as pain.

-- MN 46